3066-12-4

Usage

Uses

1. Used in Pharmaceutical Industry:
11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one is used as a potential pharmaceutical compound for [application reason]. Its unique molecular structure and functional groups may offer specific biological activities that can be harnessed for therapeutic purposes.
2. Used in Chemical Research:
11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one can be utilized as a research tool in the field of organic chemistry, particularly in the study of phenanthrenes and their derivatives. It may serve as a starting material for the synthesis of novel compounds with potential applications in various industries.
3. Used in Material Science:
The unique structural features of 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one may make it a candidate for the development of new materials with specific properties, such as improved stability, conductivity, or optical characteristics.

InChI:InChI=1/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3

Upstream product

• 80-75-1 11-alpha-hydroxyprogesterone 
• 57-83-0 Progesterone 
• 63-05-8 Androstenedione 
• 53-43-0 dehydroepiandrosterone 
• 58-22-0 testosterone 
• 521-17-5 5-androstenediol 

Downstream Products

• 25788-56-1 11α,17β-dihydroxy-5α-androstan-3-one 
• 32326-39-9 3β,11α,17β-trihydroxy-5α-androstane 
• 15375-19-6 (5α)-androst-9(11)-ene-3,17-dione 
• 1429-06-7 5α-androstane-3,11,17-trione 

Relevant academic research and scientific papers

The generation of a steroid library using filamentous fungi immobilized in calcium alginate Dedicated to the memory of Professor Sir John W. Cornforth, University of Sussex (1917-2013).

Four fungi, namely, Rhizopus oryzae ATCC 11145, Mucor plumbeus ATCC 4740, Cunninghamella echinulata var. elegans ATCC 8688a, and Whetzelinia sclerotiorum ATCC 18687, were subjected to entrapment in calcium alginate, and the beads derived were used in the biotransformation of the steroids 3β,17β-dihydroxyandrost-5-ene (1) and 17β-hydroxyandrost-4-en-3-one (2). Incubations performed utilized beads from two different encapsulated fungi to explore their potential for the production of metabolites other than those derived from the individual fungi. The investigation showed that steroids from both single and crossover transformations were typically produced, some of which were hitherto unreported. The results indicated that this general technique can be exploited for the production of small libraries of compounds.

Microbial Baeyer-Villiger oxidation of steroidal ketones using Beauveria bassiana: Presence of an 11α-hydroxyl group essential to generation of D-homo lactones

This paper demonstrates for the first time transformation of a series of 17-oxo steroidal substrates (epiandrosterone, dehydroepiandrosterone, androstenedione) by the most frequently used whole cell biocatalyst, Beauveria bassiana, to 11α-hydroxy-17a-oxa-d-homo-androst-17-one products, in the following sequence of reactions: 11α-hydroxylation and subsequent Baeyer-Villiger oxidation to a ring-D lactone. 11α-Hydroxyprogesterone, the product of the first stage of the progesterone metabolism, was further converted along two routes: hydroxylation to 6β,11α- dihydroxyprogesterone or 17β-acetyl chain degradation leading to 11α-hydroxytestosterone, the main metabolite of the substrate. Part of 11α-hydroxytestosterone underwent a rare reduction to 11α-hydroxy- 5β-dihydrotestosterone. The experiments have demonstrated that the Baeyer-Villiger monooxygenase produced by the strain catalyzes solely oxidation of C-20 or C-17 ketones with 11α-hydroxyl group. 17-Oxo steroids, beside the 11α-hydroxylation and Baeyer-Villiger oxidation, also underwent reduction to 17β-alcohols; activity of 17β-hydroxysteroid dehydrogenase (17β-HSD) has significant impact on the amount of the formed ring-D δ-lactone.

Microbial hydroxylation of hydroxyprogesterones and α-glucosidase inhibition activity of their metabolites

Microbial transformation of 11α-hydroxyprogesterone (1) with Cunninghamella elegans, Gibberella fujikuroi, Fusarium lini, and Candida albicans yielded 11α,15α,16α-trihydroxypregn-4-ene-3,20-dione (3), 11α-hydroxy-5α-pregnane-3,20-dione (4), 6β,11α- dihydroxypregn-4-ene-3,20-dione(5), 11α-hydroxypregna-1,4-diene-3,20-dione (6), 11α,17β-dihydroxyandrost-4-en-3-one (7), and 11α,15α-dihydroxypregn-4-ene-3,20-dione (8). On the other hand, microbial transformation of 17α-hydroxyprogesterone (2) with Cunninghamella elegans and Fusarium Uni yielded 11α,17α- dihydroxypregn-4-ene-3,20-dione (9), and 17α-hydroxypregna-1,4-diene-3,20- dione (10). The structures of the metabolites 3-10 were deduced on the basis of spectroscopic methods. Compound 3 was identified as a new metabolite, which exhibited a promising inhibitory activity against the α-glucosidase enzyme.